Upcoming Events

Embrace the allure of our Eastern Shore haven, where each passing season ushers in its own tapestry of charm and adventure! As we peer into the unfolding year, we're excited to present exciting happenings and unforgettable moments. Whether you're drawn to the vibrant hues of spring's awakening, the spirited festivities of summer's peak, the rustic warmth of autumn's embrace, or the magical enchantment of winter's frost, there's an experience tailored to enchant every soul. Navigate below to find the ideal time to plan your stay.

Winter

Midnight Madness

Step into the magic of Midnight Madness the first weekend of December in St. Michaels. Our charming shops extend their hours, welcoming you with festive refreshments, delectable snacks, and exclusive sales. Every purchase at participating businesses brings you closer to winning delightful gift baskets, adding to the joy of the season.

Christmas in St. Michaels

Experience the magic of Christmas in St. Michaels from December 13th to 15th! Join us for a weekend filled with joyous celebrations as our picturesque town comes alive with holiday spirit. Don't miss the enchanting Talbot Street Christmas Parade and the dazzling Lighted Boat Parade, where the waterfront sparkles with festive cheer. Throughout the town, discover a plethora of merry festivities to delight in with loved ones amidst the festive atmosphere of Christmas in St. Michaels.

Spring 2025

Easter

Hop into Perry Cabin this Easter for a brunch celebration like no other! Join us for a delightful feast with Easter egg hunts alongside the beloved Easter Bunny. Gather your family and friends for a day of joy, delicious food, and cherished memories.

Eastern Shore Sea Glass and Coastal Arts Festival

Save the date for the upcoming Eastern Shore Sea Glass and Coastal Arts Festival, taking place on Saturday, April 12th and Sunday, April 13th at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland. This Spring Edition promises an extraordinary showcase of coastal craftsmanship, with over 90 exhibitors presenting a diverse collection of jewelry, home décor, art, and more.

mother doing up the wedding dress of her daughter

Mother's Day

For Mother's Day, celebrate the amazing women who deserve to be pampered! Show your love by gifting them an unforgettable experience at Inn at Perry Cabin, where every moment is wrapped in luxury.

Summer 2025

CBMM Antique & Classic Boat Festival and Coastal Arts Fair

Plan ahead for the 37th Antique & Classic Boat Festival at the Chesapeake Bay Maritime Museum, happening June 13–15! Enhance your experience with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat. Visit here for event details and highlights.

Independence Day

Join us for Fourth of July and enjoy front row seats to the St. Michaels' stunning fireworks display on Saturday, July 5th.

Plein Air Easton

Plein Air Easton, celebrating its 21st year July 11 - 20 2025, is the largest juried plein air painting competition in the U.S and a perfect excuse to plan a visit. Hosted by the Avalon Foundation in Easton, Maryland, each July, it draws talented artists from around the world.